Loose Ends
by KEMLEM81
Summary: One month before she's due to get married Rory finds herself on Jess's doorstep looking to tie up her loose ends before her wedding day.
1. Chapter 1

_**I deleted this story a little while ago for personal reasons but have decided to share it again. Apologies if you thought I'd finally written something new but you've already read this story. I still have sequels for FT and ISWAT in the back of my mind but have not found the thread yet to start either. One day :)**_

 _ **A/N this idea came to me and I decided to see how it plays out.**_

 _ **The time frame doesn't really matter except that this is post finale and everything that happened in the show happened and Lorelai and Luke got married at some point between then and now. This idea may seem completely implausible but I can imagine it from their perspectives and fiction is about exploring other worlds or choices or experiences you would likely never venture into yourself.**_

 _ **Anyway, enough from me and on with the story.**_

* * *

 **Loose Ends**

"So we're really doing this then?" Rory asked, her arms wrapped around her soon to be husband's shoulders.

"Yes. We're really doing this. We want to start our life together with no regrets right? That's what we agreed," her fiancé affirmed, tightening his grip around her waist and leaning down to kiss her. "Two weeks to tie up loose ends, no questions asked."

This arrangement may have seemed odd to outsiders but the idea had been discussed and debated and detailed and decided over the last month following a massive fight between the couple. It had been Adam's suggestion and Rory could see the merit in it. They had met at a time when they were both still finding their path and had each made their share of sacrifices for each other. Commitment wasn't the issue here, they loved each other and they were looking forward to starting their life together as husband and wife a month from now but they were also open enough with each other to know there were facets of their old lives they needed to say goodbye to. For Adam that meant heading home, back to Vancouver and everything he'd left behind there two years ago when he moved to New York for a job. Rory had less distance to travel but further to go to tie up her loose end.

"So I'll pick you up here on the 27th?" Rory kissed him again, still wrapped in his embrace.

"2pm," he deepened the kiss, uncaring about the crowds of people milling around them.

"And we're really doing this?" Rory asked him again, doubt beginning to gnaw at her insides.

"One month from now I'll be all yours and you'll be all mine and there will be no doubt in either of our minds that it was the right decision. We need to do this Rory. You know we do. We rarely fight over anything but when we do these are the scars we rip open. This is about finally healing those scars so we don't spend the rest of our lives together tearing them open and patching them up. I know you better than anyone Rory. You know how much I love you. I know how much you love me. You go put your past to bed and I'll do the same with mine," Adam assured her.

He looked over his shoulder to check the time until his flight then looked back at Rory, searching for reassurance in her eyes. If he was being completely honest with her he wouldn't be leaving her but he knew she had unfinished business with someone she called her cousin and he'd be damned if he spent the rest of his life worrying over the hold the brooding writer had on her. He remembered the saying about setting the one you love free and seeing if they come back to you- this was his only way of knowing she was truly his.

"You'd better get going mister, can't have you missing your flight," Rory teased, attempting to lighten the mood but quickly becoming serious again. "I love you Adam."

"I love you Rory. I'll see you in two weeks," he placed a final kiss on her forehead before lifting his satchel back over his head to rest at his hip, the strap across his chest.

Rory allowed him to let her go and watched as he walked away from her, disappearing amid the crowd.

* * *

Rory let out a heavy sigh and tried to calm the nerves that were quickly overtaking her body, spreading from the inside out. She walked back to where she'd parked her car earlier that morning with her own bags packed, ready, in the back seat. She sat in the driver's seat but rather than pulling her keys out from her purse she retrieved her phone instead.

"Um, hi, it's me Rory," she stammered down the line once the call connected and she heard the "hello?" on the other end.

"Hey, you on the road yet?" he asked her, as if it were any other ordinary day and this was any other ordinary conversation. Of course, to him it was, Rory hadn't told him the real reason she was coming to visit, she'd cross that bridge if and when she needed to.

"Just about to leave, I should be there in a couple of hours," she confirmed.

"Well, I'll make sure to have a vat of coffee ready for you when you arrive. Remind me again what time your thing is tonight?" he asked her.

"Oh, actually, I decided not to go to that after all," Rory chewed on her bottom lip while she waited for him to respond.

"Huh, okay. Wasn't that why you were coming to Philly in the first place?" he probed.

"Well, that and the cheese steaks," Rory really needed to end this line of enquiry now.

"Okay," Rory could hear the curiosity in his voice but chose to misinterpret it for now.

"I can still stay with you, right?" she asked.

"Sure, of course. How you choose to spend your time here is up to you," he reassured her.

"Okay, well thanks. I'll see you in a couple of hours," she felt like she was repeating herself now and that was a sure sign she needed to wrap things up.

"I'll be right where you last left me," he answered, somewhat cryptically.

She put her phone back into her bag and took her keys out instead, pressing the bulky black headed one into the ignition and turning it. She fastened her seatbelt and turned up the radio and made her way out of the carpark. Jess's words echoed in her mind as she drove: _how you choose to spend your time here is up to you_. She had two hours to think about how exactly she would choose to spend her time but he was wrong about one thing, it wasn't up to her at all, he had a part to play here too he just didn't know it yet.

 ** _A/N please share your thoughts if you feel inclined :)_**


	2. Chapter 2

Rory parked her car across the street from Jess's apartment, locked the doors and turned to walk in the opposite direction. Less than 10 minutes later she entered the old bookstore and made her way to the back corner where she knew he'd be.

"You're so predictable," she announced her arrival, watching as he continued to read, finishing the paragraph before looking up to greet her.

"There are worse things to be," he smirked up at her then closed the book, placing it back in its place in the shelf before standing up and pulling her into his arms for a hug.

"So, where's the vat of coffee I was promised?" Rory asked, stepping away, out of his arms.

"Here," Jess turned back to the corner and lifted a thermos flask from the floor. "Should still be hot."

Rory carefully unscrewed the lid and inhaled the glorious aroma letting out a tiny moan as she did, covering her mouth in embarrassment when she realised it then taking a sip in an attempt to further cover her discomfort.

"Hey, no need to be embarrassed, I'm well aware of your secret love affair with the hot, dark type," Jess teased her.

Rory almost choked but somehow managed to swallow. She returned the lid, screwing it firmly back into place, and turned her back on Jess to examine the books surrounding them.

"Seeing as you no longer have plans tonight do you want to do something together?" Jess asked her.

"Um, yeah. That would be nice," Rory nodded but kept her eyes on the books.

"Any ideas?" he asked. She selected a book from the shelf and turned to face him.

"Can we just order pizza and watch a movie?"

"Okay. Shall we head back soon and you can see if I've got anything you want to see?" he asked.

"Sure, just let me pay for this," Rory agreed.

Jess took the thermos from her to carry as she made her way to the counter to pay. She turned back to look at him and found him smiling his half smile at her, a curious look in his eyes. She thanked the cashier and tucked the book under her arm and walked to the door, stepping out into what was left of the afternoon light with Jess following closely behind her.

They walked back in the direction she'd come and Jess helped her lift her bags out of the car. They shared the load between them and crossed the road to his apartment block. Neither of them had spoken a word since the bookstore and it was Jess who broke the silence now.

"Rory? Why are you here?"

"Tying up loose ends," she told him honestly.

"What the hell does that mean?"

"I'm not so sure of that myself, I just knew this was where I had to be to do it," she locked her gaze on his, trying but failing to decipher what she found there.

They stepped out of the lift and crossed the small hallway to Jess's front door. The air suddenly thick between them. The comparative ease of the bookstore now gone.

"Aren't you getting married in a month?" Jess asked after depositing her bags in the guest room. Rory followed him in and sat on the chair in the corner, remembering the last time she'd stayed here. Adam had been here then too. She'd been relieved when they'd discovered common ground, aside from her, and became, if not friends then at least comfortable acquaintances.

"Adam knows I'm here if that's what you're asking," Rory admitted. She hadn't exactly told Adam where she was going but she knew he'd know.

"I don't know what I'm asking Rory or what I should be asking," Jess looked at her blankly, trying to process the situation. "I'm going out for a while. Unpack, take a shower if you want. I'll get the pizza on my way back. You know where the DVDs are, pick something."

"Okay," Rory agreed quietly, knowing he was leaving because he needed space.

"Tomorrow Rory. You're going to explain this all to me tomorrow," he gestured at the bags carrying far more than was necessary for a weekend trip.

Rory sat in the chair staring at the lamp in the corner long after she'd heard the door slam behind Jess as he departed. She eventually shook herself out of her daze and opened one of her cases to retrieve her old comfy YALE sweats and her toiletry bag and went to take a shower.

* * *

It was well past dark when Jess finally returned. He placed the pizza boxes on the coffee table in front of the television then took his place on the opposite end of the couch from Rory.

"So, what did you choose?" he asked her as he reached for the remote to start the movie.

"Once," she looked at him briefly before returning her attention to the food.

"Once it is then," Jess pressed play and let the sounds of the film fill the room.

She could feel him nodding beside her but kept her eyes on the screen. They ate and watched and Jess teased her when she teared up she teased him when he started humming along and for 90 minutes they were comfortable with each other again.

"I've got some work to do," Jess told her as he rose from the lounge, the credits still rolling on the screen. When he lifted his arms over his head to stretch Rory turned her head away so as not to stare at the smooth muscles of his abdomen revealed by his shirt riding up.

"I think I'm just going to go to bed," Rory looked back at his face now. "Thanks for letting me stay."

"You know you're always welcome here Rory. Have a good sleep and we will be having that talk in the morning," Jess gave her a brotherly hug, ruffling her hair before releasing her.

"Goodnight Jess."

"Night."

Rory spent the next several hours trying to decide how exactly to explain herself to Jess, eventually drifting off to sleep not long before the sun began to rise.


	3. Chapter 3

It was almost noon by the time Rory surfaced. She tiptoed around the quiet apartment until she discovered a note from Jess on the table next to a brown paper bag and a now cold to go cup.

 _I figure you're probably staying longer than the weekend so I've gone out for groceries. Enjoy your breakfast._

 _J_

She heard his key in the door as she finished off the last of her coffee, suddenly aware of her attire but also realising it was too late to remedy it so instead she pulled the light fabric of her robe tighter and secured it closed with the belt. It wasn't as if he'd never seen her in her pyjamas before but the conversation they needed to have was one she needed to be fully clothed for.

"Hey, afternoon sleepyhead," Jess greeted her, lifting the bags of food onto the counter.

"Look at you being all domesticated, buying groceries. Is that a tomato? And carrots too? When did you turn into Luke?" Rory stood beside him and began to nosy her way through the items he'd bought.

"Are we really going to have this discussion again Gilmore?" Jess began to unpack the bags, filling the refrigerator with a variety of colourful items, some of which Rory had never seen in real life before.

"I just find it so amusing that you're a proper grown up now. I guess I should be used to it already. You never do cease to surprise me though Jess," Rory leant on the counter, watching as he moved around the kitchen automatically, retracing steps he was obviously used to taking. This was the real Jess she was observing in this moment.

"What's that smile for?" Jess closed the pantry door and turned to find Rory watching him.

"Are you happy Jess?" she asked.

"Well I'm not unhappy, does that equate to the same thing?"

"I guess."

"What about you Rory? Are you happy?"

"I think so."

"Have you decided how you're going to explain why you're here?" Jess asked then pulled out a chair to sit down at the small kitchen table.

"Almost."

"Your lack of words is leading me to think otherwise," Jess told her honestly, his tone soft and encouraging.

"Can you wait here? I just need to get dressed first," she blushed as his eyes took in her thin cotton robe no doubt noticing the fitted nightdress it was poorly concealing. Damn Adam and his abhorrence for flannel pjs.

"How about I make us some lunch? Sandwiches good for you?" Jess offered.

"Will you make me eat the green stuff?" Rory hedged.

"Possibly," he smiled his rare Jess smile at her and she found herself retreating out of the suddenly too small kitchen at the sight of it. She reached the doorway to the guest room, stepped inside then turned back to see him still sitting where she'd left him, watching her with a bemused look on his face now. She shut the door and quickly went about getting dressed then grabbed the notes she'd written last night from where she'd left them on the bedside table and returned to the kitchen.

"I'm ready now," she announced.

Jess had his back to her, still assembling their lunch at the bench. He quickly finished and sliced the sandwiches in half, placing the two plates opposite each other at the table.

"Drink?"

"Um, just water is fine," Rory answered and he grabbed two bottles from the fridge placing them on the table before sitting down. Rory followed his lead and sat too. "This looks great Jess, thank you."

"You brought notes?" Jess asked, his eyes scanning the pile of paper on the table next to Rory.

"They're more of a prop really," she admitted. "The thing is Jess, I know why I'm here but I don't know what it will entail and I know that that doesn't make much sense if any at all but it's the best I can come up with."

"So why are you here then?"

"To..."

"...tie up loose ends. Yeah, I already got that much yesterday Rory." Jess's voice was still calm and even but Rory knew it would soon lead to exasperation if she didn't find some way to say what she needed to say.

"Adam and I are getting married in a month."

"I know, I already RSVP'd."

"We are really happy Jess. We rarely ever fight but when we do it always comes down to aspects of our past that we never resolved. I'm here to try and resolve mine and he's in Vancouver trying to resolve his so we can start our life together..."

"...with all the loose ends tied in a nice neat little bow?" Jess practically spat out the words. "I'm guessing the fact that you're here, in Philadelphia, with two suitcases and a satchel makes me one of your loose ends?"

"One of the cases is mostly books..." Rory couldn't meet his eyes let alone admit to him that he was right. Now that it had been spoken out loud it seemed absurd, insulting, hurtful. "You're not one of Jess, you are the only. You're the ever present what-if in the back of my mind. If you want me to leave I'll leave. I guess I just came here because I needed to know for sure that Adam is the man I'm supposed to spend the rest of my life with."

"Geez Rory, how can you put this on me? Are you just here for some kind of twisted booty call to make sure you've made the right choice? You and I both know that has never been a problem between us. Did you even stop to wonder how this might affect me? It always ends up the same Rory. One of us always walks away and there's a reason for that." Jess leaned back in the chair, tilting his head back as he ran his hands through his already dishevelled hair. He sat back up straight and looked across the table, his eyes locking on hers, neither one of them game to speak for fear of what might come out.

"Do you want me to leave?" Rory broke the silence.

"No," Jess admitted.

"So, what now then?" she asked.

"Shouldn't I be asking you that?" Jess looked at her incredulously, still reeling from her revelation.

"Maybe we should eat?"

Jess simply nodded and picked up half his sandwich, forcing himself to chew and swallow despite the sick feeling that had settled at the pit of his stomach. Was he willing to take a chance on Rory again knowing full well she could be marrying someone else in a month? Was he willing to miss out on chance to be with her one last time, even if just for a brief moment in time?

"So your second case is full of books, huh? I'll agree to let you stay if you let me have whatever I like," Jess's mind spoke before his heart had made up its mind.

Rory blushed at his choice of words and continued to eat her sandwich while memories of what Jess had liked in the past rolled through her mind.


	4. Chapter 4

**_7 years earlier_**

"So you mean to tell me you and I are still both single at the same time?" Jess asked her, a devilish smirk tilting his lips.

"Too bad we're also now technically related," Rory pointed out even though she felt that detail was arbitrary and somewhat ridiculous.

"I was never one to shy away from taboos," Jess reached across the table and took her hand in his, linking their fingers together.

"And you always did bring out the rebel in me," the skirt of Rory's bridesmaid dress rustled as she moved her chair closer to his, enjoying the familiar weight of his arm as he placed it around her shoulders.

"Where are you staying tonight?" he whispered in her ear despite all the other wedding guests being long gone.

"Home," she answered, resting her head against his shoulder, watching their hands, still connected on the table in front of them. "Where are you staying?"

"The Dragonfly," he kissed the top of her head, breathing in the scent of her as he did. He wondered how long it would take to forget it this time.

"Which room?" she asked

"Guess." he brushed her hair aside and kissed the side of her head.

"The honeymoon suite?" she knew he'd have gone for the most private room available.

"Shall we?" he let his lips trail down to her smooth soft cheek.

"Taxi?" she asked, trying to conceal the affect he was having on her.

"Walk?" he covered her mouth with his but only for a second.

Rory stood up from the table and adjusted her dress. Jess stood up from the table and took his jacket from the back of his chair to drape around Rory's shoulders before kissing her again.

By the time they reached the inn Rory's shoes were in her hand and all trace of lipstick was gone from her face. Her fancy updo was completely undone and the buttons down her spine partially so. Jess's face bore the crimson evidence of its connection with hers and his hair was a mess most would consider the norm for him had they not seen how it was groomed earlier for his role as best man. They slipped into the private suite unobserved and put the do not disturb sign on the door before locking themselves in. Tonight there would be no interruptions.

"How long are you staying?" Rory asked as she removed his jacket, hanging it on a hook on the back of the door.

"Just tonight," Jess removed his tie and begun to undo his cufflinks. "When do you get back on the road?"

"Two days from now. New York," she undid his shirt buttons one by one.

"New York's pretty close to Philadelphia," Jess let his shirt slide down his arms to fall on the floor behind him.

"I heard that rumour too," Rory kissed him as he undid the rest of her buttons. He stood back and watched as she wriggled her hips slightly and the gown fell down creating a pool of blue satin at her feet. He held his hands out to her and she took them, stepping out of the circle of fabric.

"Maybe I could stay a little bit longer and then take you there myself?" he suggested, kissing her neck as he trailed his hands up her back in search of the clasp on her bra.

"We've been here before Jess. There will never be enough days to string together. I'll have to leave again eventually," she sighed as she felt the cool air on her bare skin.

"I'm not asking for forever," Jess reminded her, undoing his belt and removing his socks and trousers.

"Let's just focus on the here and now and deal with tomorrow tomorrow," Rory reasoned, wrapping her arms around his bare torso, enjoying the feeling of his warm bare chest against her cooler skin and the way the contact quickly made her skin blush with a matching heat.

"But it is already tomorrow," Jess reminded her before covering her mouth with his once more and guiding her back toward the bed.

* * *

Rory was woken by the sound of the shower the next morning. She wrapped herself in the top sheet and padded across the plush carpet to the bathroom.

"Planning a quick getaway?" she dropped the sheet on the floor and stepped into the shower with Jess.

"Check-out is in 15 and I don't want to drive all the way back to Philly without taking a shower first," he kissed her across the stream, water droplets spraying haphazardly around them.

"What if you stayed another day?" she asked him as she lathered shampoo in her hair, washing away yesterday's hairspray.

"Yeah, I decided that wasn't such a good idea after all," Jess gave his hair one last rinse then stepped out of the cubicle.

"Oh really? One night was enough for you then?" Rory rinsed her hair then coated it with conditioner.

"You know the answer to that Rory. You also know it doesn't change anything, you said so yourself. You're right, it's tomorrow now and I'm choosing to walk away before it gets any harder to," Jess wrapped a towel around his waist and left the bathroom to get dressed and gather his belongings together.

Rory finished washing her hair and switched off the taps, wringing the excess water out of her long hair before stepping out onto the mat. She wrapped one towel around her head and another around her body and stepped out of the bathroom to find Jess sitting on the end of the bed fully dressed, shoes and all, his packed bag on the floor by his feet.

"You lied about the time didn't you?" she already knew the answer.

"It's my turn to leave first," he reminded her. The last time,which was in fact the first time, it had been impossible for him to leave first because she was in his apartment and she was the one with a bus to catch, places to go, candidates to see.

"At least let me kiss you goodbye," Rory pleaded as he rose from the bed.

"A deal's a deal," Jess agreed, closing the gap between them and wrapping his arms tightly around her. The towel on her hair unraveled and fell to the floor as the force of his mouth on hers tilted her head backwards.

"I love you Jess, drive safely," Rory gave him a tight squeeze before releasing him.

"I love you Rory, I'll call you when I get home," Jess promised her even though they both knew he wouldn't.

"Goodbye Jess."

"Goodbye Rory."

They parted with goodbye because a deal is a deal, no matter how difficult it seemed to stick to at times. She knew he'd call her in a week. He knew that she knew and so he would wait that week. Their lives were separate books whose plotlines occasionally crossed over. It was time for them to get back between their own separate covers again now. Until next time.

 ** _A/N thanks for reading if you're still with me. Let me know what you think if you feel inclined :)_**


	5. Chapter 5

**_A/N thank you to my lovely reviewers, I promise I will reply to each one individually soon, I've not been well and want to reply properly when I can think straight._**

 ** _Present_**

"How long are you expecting it to take to tie up your loose ends?" Jess asked Rory over breakfast the second morning of her stay.

"Two weeks," Rory looked up from her eggs to see him watching her.

"That's very specific," his eyebrows rose dubiously. "What if it's not done by then?"

"Well, I guess that's kinda the point isn't it?"

"I'm not sure I follow."

"If I can't work out how to be content to just be friends with you by the end of two weeks then time will become irrelevant because the deadline will no longer exist," Rory spoke frankly. He was right, two weeks was not a lot of time and she didn't want to waste anymore of it by tiptoeing around the myriad of issues she'd come here to resolve.

"No longer exist as in the wedding would be off?"

"Would you marry a woman who was still in love with another man?" Rory let slip.

"No." Jess answered automatically. "Wait a sec, what did you just say? Am I the other man? Are you telling me you're still in love with me?"

"Please Jess, calm down," Rory placed her hand over his across the table. "In answer to your questions yes and I honestly don't know. That's why I'm here."

"Does it matter whether or not I'm in love with you?" he asked, angry and confused.

"Are you?"

"Answer my question first Rory."

"Of course it matters Jess. You know I love you and I never want to do anything to hurt you."

"This seems like a twisted way of showing it," Jess hung his head in his hands. She was here to heal her own scars and was likely to rip him to shreds in the process.

"Everything has always been so complex between us Jess. Maybe this will be good for both of us. We can figure out once and for all if we could make this work or if we can finally set each other free. Don't you think we both deserve resolution after all these years?"

"Well I'm glad you went with a less cliched term than closure," Jess returned his palm to rest atop hers and gave her hand a gentle squeeze. "How do we do this then?"

"I guess we just see what happens and figure it out along the way?"

"Okay."

"You didn't answer my question," Rory reminded him.

"I guess that's something I need to figure out too."

* * *

Rory found herself alone for most of the day as Jess buried himself in his office under the guise of work. She wandered the streets of Philadelphia window shopping and daydreaming herself into a life here with Jess. It wasn't too big a stretch for her to imagine but then she thought about the life she'd already been living with Adam in New York and she knew for a fact she was happy there. There were reasons she and Jess had never worked out despite their undeniable physical compatibility and shared interests but with Adam there was that little something more that she and Jess had never even attempted to look for amid the distractions of their separate lives and their occasional rendezvous over the years.

Jess had to get away from her again, this was all a bit too much for him to take in. He had told her he had work to do and locked himself in his office where he sat staring at his blank computer screen trying to answer her question. He loved her. He'd always loved her. At some point it had evolved into a platonic kind of love. She was his closest friend. Sometimes it seemed a fine line to tread but he hadn't thought about crossing back over it again for a long time now. Two years, give or take. The day she'd called him and told him she'd met someone was the day he'd given up on any future with her. When she'd called to tell him she was engaged he'd nailed the door on that part of his life shut and buried himself in his writing instead.

Rory called out to Jess as she let herself into his apartment just after 5pm. She had several shopping bags in her hands because window shopping just wasn't cutting it and she'd caved. She placed a small brown paper package on the kitchen bench then took the rest of her purchases through to her room. She still hadn't heard any response from Jess so she planned to take a shower and relax in front of the TV until he surfaced.

Jess heard the shower running and left his office for only the second time that day. He took a bottle of water from the fridge and swallowed half of it before screwing the lid back on. When he noticed the brown paper package on the bench he smiled and when he stepped closer and saw she'd written his name across the front of it he opened it, removing the book from inside.

Rory took her time in the shower, enjoying the heat of the water on her tired muscles as she washed the city grime away. The door to Jess's office was open now but a quick search of the apartment revealed its owner to be missing. Rory went to get a drink of water from the kitchen and stopped when she saw the opened package on the bench and Jon Krakauer's thin paperback sitting on top of it. _Oh Jess, you were supposed to wait for me so I could explain._ Rory tore of a piece of the bag and wrote in it then folded I over the front cover to secure it in place. She sighed out loud in the empty space then made herself a simple dinner from Jess's well stocked pantry and went to bed early.

* * *

It was 2am when Jess returned home, the irony of the timing not lost on him. The book was still where he'd left it but there was now a note attached to the cover that hadn't been there before.

 _"Some people feel like they don't deserve love._

 _They walk away quietly into empty spaces,_

 _trying to close the gaps of the past."_

 _R x_

Jess left the book on the bench but took the note with him and went to bed.

 ** _A/N the things that don't make sense right now aren't supposed to, they will very soon I promise :)_**

 ** _Please pay attention to the time stamps heading each chapter to save confusion. This story is written like a puzzle and will continue to go back and forth. Let me know if you need me to explain anything :)_**


	6. Chapter 6

_**The First Time - 7 years earlier**_

"Yeah?" he barked down the phone, having been woken from his sleep by its insistent ringing.

"Um Jess? It's me."

"Rory?"

"Are you home?"

"Where else would I be at two in the morning?"

"Can I come over?" Rory listened to silence on the other end of the line then breathed a sigh of relief when he finally spoke again.

"Sure. How far away are you?"

Rory pressed the intercom and could hear him groan as he made his way out of his bed and across the small apartment, still holding the phone.

"That close huh? I guess I'd better let you in then," he hung up on her and buzzed her in. He was standing waiting at the door for her when she reached it.

"Hi," she greeted him almost shyly as she carried her bags through his doorway.

"You know where everything is, you can explain yourself in the morning, I'm going back to bed," Jess shut the apartment door and locked it then crossed the living space to his own room and slammed the door behind him.

"Thanks Jess," Rory whispered redundantly across the silence.

* * *

Jess was reading in the lounge when Rory stepped out of his guest room the next morning.

"Sleep well?" he asked her.

"I really did," Rory assured him. "Sorry about..."

"Hey, I always tell you you're welcome anytime right?"

"Yes, but I'm sure you never expected that to include me lobbing on your doorstep at 2am," Rory shrugged apologetically.

"I figure you've got your reasons," Jess was curious but wasn't going to be the one to ask.

"Oh, I do! My roommate for the next 4 nights snores like a bulldozer and I could not for the life of me get to sleep even with earplugs! I packed all my stuff up and sat in the hotel lobby for a while and then I remembered I was in Philly and that _you_ live in Philly and so I called you and you answered and here I am," Rory explained.

"For 4 nights?"

"Would that be okay?"

"Well I can't have you suffering from sleep deprivation now can I? Especially when you more or less own that room anyway," he gestured to the doorway she'd come out of.

She knew he didn't have a lot of visitors but hadn't realised he saw it that way - as hers. It made sense to her now, the ever changing pile of books on the bedside table. The old grey shirt of his that was always in the bottom drawer for her to borrow for a nightdress. Little unspoken gestures of a friendship they had worked hard to salvage over the last year. She took a seat beside him on the couch and stole his book out of his hands, turning to the back cover to read the blurb.

"You can have it tomorrow, I'm almost done," he took the book back from her, smiling as she pouted in protest. "Hey, who's doing the favour here?"

"You are," Rory admitted with faux reluctance, letting the book slip through her fingers.

"So, what's your _schedule_ like?" Rory laughed as he practically choked over the unfamiliar word.

"We had a big function last night, free day today as it's Sunday. Monday is pretty full, Tuesday is just a morning thing and the same again Wednesday then I'm on the bus to New York first thing Thursday morning." Rory told him. "Hey, don't look at me like that, you asked!" she slapped his shoulder playfully.

"So all you evenings are free?"

"Yes. I do have to write and submit my articles but otherwise the evenings are all mine." She studied his face while he took in this information. "Are you sure this is going to be okay, me staying? If you have other plans, if you're seeing..."

"I'm not seeing anyone Rory, you won't be cramping my style. I was actually just thinking I'm overdue for some company. I've been so caught up writing these days and now I live on my own I can go weeks without actually having to speak to anyone."

"You old hermit, you!" Rory teased.

"You maybe want to go see a movie with me tonight?" Jess asked.

"I'd love that," Rory agreed. Life on the campaign was lonely for her too.

"So, are you...?"

"No Jess. Not since Logan, you know that."

"Not officially. Life on the road must offer more opportunities than my solitary existence."

"It's as if you don't really know me at all," Rory said quietly. There had been offers, she just hadn't ever felt right about taking any of them.

"I just..." Jess shook his head slightly, swallowing whatever words he had been about to speak.

"You just what?" Rory probed.

"Nothing. Look, I'm going to head out for a bit, need to get a few things. I'll bring back some lunch then maybe we can take a walk somewhere."

"Okay, that sounds nice. Thanks again for letting me stay Jess. I appreciate it."

"I know you do."

He handed his unfinished book to her and pocketed his keys and phone, tied his laces and exited the apartment.

Rory sat staring at the book in her hands and was startled when barely a minute later Jess opened the door again. She heard him rummaging in the kitchen drawer then he was standing in front of her.

"Here, you might as well keep this," he passed her a spare key. "Better off in your pocket then lost in the bottom of a drawer."

Rory took the key and held it safe in her palm, trying not to read too much into the gesture. Sometimes a key was just a key.

* * *

It was late afternoon when Jess finally returned and Rory was starving. She'd finished his book and placed it on his bedside table for him and had later fallen asleep on the couch. The smell of burgers woke her and she sat up just in time for Jess to drop a takeout bag on her lap.

"Have you moved at all since I left?" Jess smiled down at her looking much more relaxed than he had that morning.

Rory didn't bother to answer him but began to feed her hungry stomach instead.

"You still feel like catching a movie?" he asked her when she'd finished eating.

"Give me 10 minutes and I'll be ready to go," she stood up from the couch, stretching her back as she did.

They walked and talked and caught up on all the small details of the last few weeks since they'd last spoken to each other. When the sun started to set behind the buildings they made their way to the cinema, bought tickets to "Into The Wild" and selected seats toward the back of the near empty theatre. When the credits rolled they each sat their stuck in their own thoughts, neither of them making a move to leave until the usher came to sweep beneath their seats.

Jess reached for Rory's hand as they walked out into the night and she found herself thankful for the weight of it in hers and the way it tethered her back to reality somehow. She'd spent a lot of the movie thinking about the period in her life where Jess had been missing, he'd just up and vanished without a word. She squeezed his hand tighter in hers and snuggled into his side thankful that he had survived his search for something else even if she wasn't sure he'd ever actually found what he was searching for.

When Rory snuggled into his side, Jess let go of her hand and wrapped his arm around her shoulders instead. Next time he'd make sure to check what was showing before picking some random film that hit a little too close to home for his liking. He kissed Rory on the top of her head, just like he used to before his life blew up in his face and he'd run away.

"Are you okay?" she looked up at him, her eyes still glistening from the tears she'd shed during the film.

"Just thinking," he stopped walking and pulled her around to face him, wrapping his arms around her waist.

"I wonder what happened to Ron," Rory mused, wrapping her own arms around his waist.

Jess leant down and kissed her, hesitantly at first but then more deeply when he found no resistance there. They continued to make out like they were teenagers again until Rory broke away.

"What are we doing?" she asked, still a little out of breath.

"Rediscovering an age old cure for loneliness?" Jess attempted to joke but his tone gave him away.

"And you think that's a good idea?"

"I haven't felt this inspired in a long time." he told her honestly.

"Seriously Jess, I think we need to stop, take a moment to process this."

"Shall I get the paper and pencils and start ruling up some columns?"

"Maybe..." Rory looked at him pensively, already constructing a list in her mind.

"Do you love me Rory?" Jess's arms were still around her waist, not giving her any opportunity to run away.

"I don't know."

"I'm not asking if you're in love with me."

"Well I guess, yes, I do love you. You're one of my best friends, despite everything we've put each other through."

"Good. I feel the same. I love you Rory."

"But I don't want to do anything to screw up what we have now. It's too important to me."

"To me too. Maybe you're right, we should sleep on it."

"I'll show you my pro con list in the morning."

Rory hugged Jess before letting him go. She held his hand in hers and they walked the rest of the way back to his apartment in silence.

Once they were back Jess kissed her goodnight then pushed her into the guest room, shutting the door behind her before retreating to his own room and locking himself in. He sat on the end of his bed, head in his hands. _What the hell were you thinking?!_

Rory sat on the chair in the corner, pen and paper in her hands. _Why the hell did I say no?!_

* * *

Jess was woken by a knock at his door. He checked the time and groaned but got up and opened the door anyway.

"Is this your favourite time of day Gilmore?" he rubbed the sleep from his eyes then tried to adjust to the dim light.

"It's when all my best thinking happens," she admitted. She held out a single piece of paper for him to read and watched, slack jawed, as he crumpled it up in his hand and threw it across the room. "That was..."

"Your list? I realise that. Given that you're here at my bedroom door in the middle of the night I'm just going to guess what you decided. Feel free to stop me if I got it wrong," Jess grabbed her by the sides of his old grey shirt and pulled her into his room, spinning her around to deposit her on the bed and covering her body with his.

" _Happiness is only real when shared_ ," he whispered in her ear then began to kiss all the spots he'd kissed in the past and when he was finished rediscovering all of them he began to explore new territory. They kept each other up until the sun rose, then fell asleep in a tangle of limbs and hair and cotton.

 ** _A/N I'm sorry if some readers think this is out of character for Jess but in this period of time I see him as a deeply lonely person and the movie they saw shook him up and made him want to take a chance and reach out and grab something tangible to push that feeling away. thanks for reading :)_**

 ** _On a side note, I've got a first chapter flitting around in my mind for a sequel to It Started With A Text and hope to have it ready to publish next week. Yay! If you haven't already read it, check it out on my profile - if you love literati as much as I do I'm pretty confident you'll enjoy it. :)_**


	7. Chapter 7

**_Present_**

Jess had managed to avoid her for three entire days. Rory was on the verge of packing her bags and leaving when he slid the note under her door. She opened the envelope and read the brief card inside inviting her to dinner with him that night. She checked the time discovering it was already after 6 and he was due to pick her up at 7. She examined her hair in the mirror and decided it would do and chose a simple black dress from the small selection she'd hung in the closet, favouring it for its versatility considering she had no idea where Jess was taking her. She touched up her makeup and buckled the thin straps on her black strappy heels and stood in front of the mirror to assess the overall effect. It would have to do, she shrugged at her image and turned away.

When a light knock came at the door she was startled and dropped her purse to the floor. She scrabbled around to pick up its contents that were now spread across the carpet, some having flown under the bed. A second knock came and she stood up and straightened her dress down over her thighs then walked across the room to open the door.

"Hi," Jess greeted her. His face was shy and guarded but he looked sharp in his suit jacket and dark jeans. His eyes travelled quickly over her body before he spoke again. "You look nice. Are you ready to go?"

Rory just looked at him incredulously. He'd avoided her for 3 days and now was acting as if nothing was amiss. Two could play at this game, at least she thought she could.

"You look nice too. Handsome. I'm ready," she slipped her hand through his proffered arm and allowed him to lead her out of the apartment.

When they reached his car he held the door open for her and closed it behind her once she was safely inside. She was confused by whatever game he was playing. He wasn't acting like himself at all.

"Are you okay Jess?" she asked him when he was sitting in the driver's seat beside her, his keys still in his hand.

"Yes Rory. Are you okay?" he looked across at her, his poker face fixed firmly in place.

"I'm a little confused but otherwise I guess I'm okay." Rory watched as the facade dropped and waited for him to explain.

"I've done a lot of thinking over the last few days Rory. Mostly about all the things I would've done differently if I had a second chance. When you told me why you were here I was angry. I can't even begin to explain it Rory but it was something akin to the way you made me feel the first time you came to Truncheon. It took me a long time to move on from that and find a way to be in your life without being the _one_ in your life. I had to find a different way to fit with you and I did and somehow we made it work. It wasn't always easy but it was what it was and it did work and then you come here and you lay this fucked up plan out on the table and I don't know what you want from me. You've blurred the fucking edges and I don't know where I fit with you now. There's no list of rules for me to follow this time," Jess paused for a moment, resting his forehead on the steering wheel. "This is me attempting to see this as a second chance and do things differently and see if it changes anything. Most normal couples go on dates so I figured that was a good place to start."

Rory blinked back the tears that were burning her eyes before he could notice their presence. She should have known better than to come here and do this to him. Jess wasn't just some old boyfriend, he had become an irreplaceable support in her adult life and here she was risking it all.

"I'm sorry Jess. I'll pack my bags and leave if you want me to. I clearly didn't think this through. I never want to hurt you. I love you too much to ever want that," Rory undid her belt and went to open the car door.

"Hey," Jess stopped her with a gentle hand on her arm. "The damage is already done Rory. No point running away now."

Rory refastened her belt and nodded in silent agreeance as Jess started the engine and drove them to their dinner destination.

By the time the waiter had taken their order and filled their water glasses they both seemed to have relaxed. Jess turned down the wine list and Rory did the same. Alcohol was not going to help in this situation, it would only make matters less clear than they already were.

They made it through all three courses with very few lapses in conversation and no uncomfortable ones. If the circumstances surrounding them being there could be ignored it would have been considered a perfect date.

As Jess drove them home Rory's nerves began to build again and she had to grasp her hands in her lap to keep them from shaking. They parked the car and then everything happened in reverse to the start of the evening as Jess opened her door and helped her out of the car then lead her back into the lift and through the apartment door. He stopped when they reached her door and, in keeping with the pretence of this being their first proper date, he leant down and placed a gentle kiss on her lips then let her go.

"Goodbye Rory."

"Goodbye Jess."

Behind separate doors on separate beds they lay in identical positions, both remembering the evening they'd just shared, both falling asleep with silly grins on their faces, both feeling 17 again.

 ** _A/N please consider leaving a review so I know if you're enjoying this story or not. Thanks for reading :)_**


	8. Chapter 8

_**The Days That Followed The First Time**_

Jess awoke to not only an empty bed but an empty apartment. Rory was gone but her bags were still in the guest room so he went back to bed knowing it would be hours before she returned. He tried to get back to sleep but thoughts of the night before wouldn't let him so he chose to indulge in them rather than fight them.

Rory may as well have stayed home that day for all the attention she gave at the speeches. Her mind was stuck replaying last night and she gave in when they broke for lunch, feigning a headache to anyone who might miss her when they reconvened for the afternoon.

Jess was still in bed when he heard her key in the door. He briefly considered getting up and dressed but decided against it and settled his head back onto his pillow, pretending to read the last chapter of the book Rory had so considerately left on his bedside table. He smiled at the thought of her sneaking into his room while he was out. He wondered if she'd snooped but figured he'd have heard about it by now as she would have no doubt made several interesting discoveries.

"Jess? Are you home?" her voice rang out through the apartment.

"I'm right where you left me," he answered.

Rory appeared in the doorway and observed that he was in fact exactly where she'd left him and as she'd left him. She could feel the blush rising in her face and wondered if she was ever going to grow out of that irritating trait.

"You look tired," Jess observed.

"Couldn't focus so I called it a day," Rory admitted.

"Why don't you come back to bed?" Jess suggested.

Rory raised her eyebrows at him in surprise.

"To sleep Rory. You can go to your own bed if you don't trust me to keep my hands to myself," Jess reasoned.

"What makes you think it's your hands I don't trust?" Rory's blush deepened.

"Well, there's nothing I can do about that," Jess sighed in mock defeat.

"Your bed is pretty comfy and you are very warm," Rory kicked off her shoes and unzipped her trousers leaving them on the floor. She unbuttoned her blouse and dropped it next to them and crawled under the covers in her underwear and singlet.

Jess wrapped an arm around her shoulders as she snuggled into his chest.

"This is nice," Rory sighed before drifting off to sleep.

* * *

Rory napped for the rest of the afternoon and awoke to find Jess cooking dinner.

"If you tell me there's chocolate pudding for dessert I may never leave," she confessed as she walked up behind him to see what exactly he was stirring on the stove.

"Does chocolate ice cream count?" he asked as he stirred the meat sauce.

"I'll have to get back to you on that."

Rory grabbed plates and cutlery and set the table for two then sat and waited for Jess to join her.

"Do you want to talk about it Rory? You've got that look on your face and if you want to talk about it we can."

Rory was a little taken aback by his observation but he wasn't wrong, she did want to talk about it. More specifically she wanted to talk about if and when it might happen again.

Jess took a folded piece of paper from his back pocket and placed it on the table.

"Seems like there weren't many cons," he pointed out.

"No, but they are all pretty big issues on their own. Had I gone into subcategories this list would have had a very different outcome," Rory admitted.

"I'm glad you didn't," Jess came around to stand beside her and pulled her up into his arms.

"Really?"

He kissed her until her knees began to buckle then lowered her back into her chair, kissing her one last time before returning to the stove to check on the food.

"I think we need a new list now. An agreement, ground rules."

"Why am I not surprised? Can I at least serve dinner first and then we can discuss it while we eat?"

Rory nodded in agreement and turned the wrinkled paper over to the back then went to retrieve a pen from the kitchen bench. By the time they'd finished eating they had a reasonable list compiled:

 _1\. This only lasts as long as we both agree to it._

 _2\. Safety first always._

 _3\. Full disclosure of any changes in our individual relationship status._

 _4\. Full disclosure of any changes in feelings in this relationship._

 _5\. No angry sex._

 _6\. Always be respectful and call when you say you will._

 _7\. Never leave without saying goodbye._

They left the list on the table, turned the stereo up and returned to Jess's bed with the tub of ice cream and two spoons to enjoy their second night together.

* * *

The days apart flew by slowly and the nights together ever so quickly. Somehow it was Thursday already and Rory's alarm was trying its hardest to wake the lovers from their slumber. Jess was the first to react and he reached across Rory's still sleeping form to hit the snooze button. He kissed Rory's bare back then settled back onto his pillow and fell back to sleep. The second time the alarm went off it was Rory who stirred. She shut it off quickly and got out of bed as carefully as she could so as not to wake Jess.

Her bags were packed and waiting by the front door when she climbed back onto the bed beside him, less careful about her movements this time as she wanted to wake him up. She kissed the back of his neck and trailed her fingertips up and down over the exposed length of his spine until he let out a gentle contented sigh and rolled over to face her.

Jess took a few seconds to register Rory's attire.

"Time to go?" he asked her, wishing he could keep her here forever. Next time he'd buy pudding not ice cream.

"My bags are at the door, I'm just waiting for the taxi to get here," Rory kissed him gently on the lips then got up off the bed.

"So I guess the next time I'll see you will be at the wedding?" Jess asked her.

"Yes, the wedding. Sixteen weeks."

"Call me when you get to New York?"

"You know I will."

The intercom buzzed, her taxi was here. Jess got up out of bed, pulling a shirt on over his head as he followed Rory to the lift. He wrapped his arms around her and held her close, unable to find the words he wanted to speak in this moment. Rory's seemed equally lost. He let her go when the lift doors opened on his floor and watched her step inside it.

"Goodbye Rory."

"Goodbye Jess."

The doors closed and she was gone.

"I love you Rory."

Fuck. He was already breaking the rules. Maybe this wasn't such a good idea after all.


	9. Chapter 9

_**Present**_

The mood had definitely shifted between them since their date although neither of them could find quite the right words to describe how. In a way they'd just settled back into their usual level of comfort with each other, bickering and bantering and giving each other space when they sensed they needed it and enjoying the comfortable silences between them as they relaxed together with separate books. It was almost like old times but also very different. The ring on Rory's finger was a constant reminder that this was all temporary.

3 days after their dinner Rory found another note under her door. This time she picked out a pretty summer dress and cardigan and slipped her feet into some flat sandals. While she waited for Jess to knock on the door to pick her up she remembered having dropped her purse the last time and crouched beside the bed to check if she'd missed any items in her rush to answer his knock that night.

She found a pencil stub and a spare lip balm but otherwise she must have got it all. She also found a pile of books she'd never seen before, neatly stacked under the centre of the bed. She had to lift the mattress from the base and slip her arm through the slats to retrieve them. She replaced the mattress, tucking the sheets back in before sitting on the edge of the bed with the four books in her hands. Why had they been under there? Maybe there was someone else in Jess's life, these weren't exactly his kind of thing.

When Jess eventually knocked she called out to him to come in. She was almost finished the first chapter of the first book in the set and wanted to get to the end before putting it down.

"I'll just be a few minutes," she held up her hand to Jess as she heard him enter her room, her eyes never leaving the page. Had she looked up she may have noticed the way his features changed when he saw what she was reading. He sat in the chair in the corner and watched her as he waited. True to her word, she closed the book and placed it beside her on the bed a few minutes later, she always had been a fast reader.

"Good book?" he asked her.

"Interesting for sure, if we didn't have plans I'd happily stay here and continue with it," Rory stood and smoothed her dress. "Does someone else stay in this room Jess?"

"Well, Luke and Lorelai have a couple of times. Lily came to stay once over her summer break. Otherwise no, you're its most frequent occupant. Why do you ask?"

"I found these under the bed. Lily must've left them here," Rory decided.

"Probably. Only person I've ever met who loves books as much as we do," Jess agreed with her then changed the subject back to their plans. "Shall we go then?"

"I'm ready," Rory took a step toward the door.

"Bring the book if you like, I know you want to," Jess teased her. He picked it up from the bed and placed it into her hand then patted the book in his back pocket. "Can't have you stealing mine."

"Planning on getting bored on this date Jess?"

"Not at all."

He took her other hand in his and lead her out of the room and into the kitchen where he picked up a covered picnic basket from the table.

"You're taking me on a picnic?"

"Yes Rory but it's going to end differently this time," Jess promised her.

"Does that mean I get to push you in a lake?"

"No."

Rory pouted all the way to the lift until Jess surprised her with a kiss.

"Tell me about this book you found," he encouraged her.

"At first glance I didn't think it would be something I could get into but it's not your typical romance novel, it really pulled me in and I've only read about a dozen pages," she admitted.

"Romance huh? Never was much a fan of the genre myself. Too many cliches. Too many implausible happy endings." Jess started the car and pulled out into the street.

"So, where are you taking me this lovely summer evening Jess?"

"There's this place where they have trees and flowers and grass, I thought we might go there," Jess smiled across at her while she pretended to scowl at his vagueness.

It took a little while to find the park and even longer to find a parking space.

"Must be a popular spot?" Rory queried.

"I guess we're about to find out." They both got out of the car and Rory waited in the sidewalk while Jess got the picnic basket out of the back seat.

"You've never been here before?" she asked.

"No."

"So how did you find out about it?"

"Someone told me about it once, seemed like something you might enjoy," Jess reached out to take her hand and lead her down the path and through the gates to the Arboretum.

There were already dozens of blankets spread around on the various patches of grass. Jess chose an empty spot in a corner a little further away and passed two ends of the blanket to Rory to help him spread it out on the ground.

"Wow Jess, this place is beautiful, very Victorian era. Thank you for bringing me here," she kissed his cheek and settled herself down on the blanket beside him.

"There's a jazz band later too," Jess handed her a plastic cup then poured sparkling cider into it.

"This is perfect Jess. When did you become such a romantic?"

Jess ignored her question and busied himself unpacking their food instead.

"There's an extra blanket in case you get cold later," he placed it behind her.

"Still evasive I see," Rory smiled as she remembered a different picnic they'd shared almost half her lifetime ago.

They ate the food and read their books and enjoyed the last of the afternoon sun. Jess looked up every so often to watch her reaction as she read her book, smiling as she reddened at certain parts and teared up at others. Part of him felt like he could do this with her forever but he also knew life was more than picnics and jazz bands and books and movies and music. For someone like Rory life was also about family and predictability and he'd never been any good with either of those.

"What are you thinking?" Rory felt his eyes on her and looked up to examine his face in the fading light. She placed her book down and waited for him to answer her.

"Do you see yourself having kids one day?" he answered her with a question of his own.

"Yes, someday. Probably sooner rather than later. Adam and I..." Rory stopped herself from saying the rest.

"You can talk about him Rory. We can't just pretend he doesn't exist."

"Adam and I would like 1 maybe 2. We found the perfect house in the Hudson Valley but we haven't put an offer in for it yet." Rory admitted quietly, unable to meet Jess's eyes.

"Sounds like you've got it all figured out then."

"Everything but you," Rory looked at him sadly.

The band began to play and Jess packed the remnants of their picnic back into the basket and lay down on his back across the rug. Rory did the same and found his hand resting between them and tangled her fingers with his.

The stars weren't particularly clear but they both gazed upon them anyway.

Rory silently wished for reason.

Jess silently wished for release.

 ** _A/N is anyone actually reading this? Should I keep going or ditch it and focus on Future Days?_**


	10. Chapter 10

_**5 years earlier**_

It was getting pretty late and Rory was contemplating putting her book down and going to bed when her phone rang.

"Hello?"

"Hi Rory."

"Oh, Jess, hi. I haven't heard from you in..."

"It's been a while I know. Got busy."

"All part of that stupid being a grown up thing."

"It's overrated."

"Definitely."

"So, that's actually kinda why I called. I've got a few meetings with my publisher in New York next week and I wondered if I could borrow your guest room for a few days."

"Of course you can. When should I expect you?"

"Well my first meeting is Monday but if you're not busy I thought I might drive down tomorrow night..."

"So I'll have you for the entire weekend?" Rory cut him off excitedly.

"Well, yeah, if that's okay with you? It's pretty last minute. Don't want you having to change any plans on account of me."

"I have no plans. Do you still have your key?"

"Yes."

"Well I can usually get off a little earlier on Fridays but just let yourself in if you beat me home."

"See you tomorrow night then."

"See you then Jess."

"Hey Rory?"

"Yes Jess?"

"Thanks."

"Save your thanks for tomorrow. It's been a while, I've missed you."

"Goodbye Rory."

"Goodbye Jess."

Rory let the phone slip through her fingers and drop onto the couch beside her. She rested her head back and let out an elated sigh, unable to keep the smile from her face. Jess had called. She knew he would because he respected the rules they'd written over two years ago she just never knew how long it would take for him to fulfil them. She hadn't heard from him in almost three months and she had missed him. None of that mattered now though, he was coming to stay and they'd have the whole weekend to catch up.

* * *

Jess didn't even bother to knock when he reached Rory's door. He turned his key in the lock and let himself in, dumping his bags in the tiny entry way then following the sound of Rory's off pitch singing. He sat on the closed toilet in the bathroom enjoying the terrible concert, waiting patiently for her to switch off the taps and step out of the shower. He pushed her towel into her hand as it reached for the towel rack and she let out a startled scream. She wiped her face dry, realised it was Jess and began to hit him with a comb she'd picked up off the bench.

"Jess! How...what...you scared me!"

"Well I guess we're even then, your vocal stylings are pretty terrifying."

Rory wrapped the towel he'd handed her tightly around her body and grabbed a second one from the rack to dry her hair.

"I didn't expect you to be here this early," she admitted, calming down from her fright.

"I can leave and come back if you want," Jess offered.

"Or you could just get over here and give me a proper hello," Rory held her hands out to him and he lifted them to his shoulders, wrapping his arms around her waist and pulling her in for a long overdue hug.

Rory could barely conceal her disappointment when he simply kissed her on the forehead and let her go.

"Hey, don't look at me like that!" Jess noticed the frown lines forming on her forehead. "I was trying to be a gentlemen."

"Why would you want to do a thing like that?" Rory asked him.

He stepped back toward her and grabbed her around the waist, lifting her and throwing her over his shoulder and carrying her through to her bedroom.

"Well that wasn't very gentlemanly!" Rory protested but the heat rising beneath the surface of her skin showed him that she didn't mind his behaviour at all.

When he undid her towel she let out a happy sigh and closed her eyes as he kissed her from head to toe.

"I've missed you," she whispered as he rested his head on her chest sometime later. She stroked the smooth skin of his back and ran her fingers through his messy hair.

"You missed me or you missed that?" Jess ran his hand up her leg, leaving it to rest at the crease of her thigh.

"Both I guess," Rory pulled gently on his hair to make him turn his face toward her. "Three months is a long time to go without talking to your best friend."

"Best friend huh?"

"You know what I mean."

"I've missed you too Rory," he moved up her body and kissed her.

"You missed me or you missed that?" Rory threw his own question back at him as she felt him growing again against her hip.

"Both I guess." he answered her with her response then covered her body with his once more and reminded them both again what they'd been missing out on.

* * *

"Is there anything in particular you want to do this weekend?" Rory asked him as they lay together in bed the next morning. Jess's bags were still at the door where he'd left them. Empty pizza boxes littered the floor and two wine glasses sat forgotten on the bedside table. It had been an eventful night of catching up and neither of them felt any motivation to move at the moment.

"This." Jess answered her, his head half buried in his pillow.

"Besides this? We can't just stay in bed all weekend," Rory pointed out sensibly.

"Why not?"

"Well, because..."

"Face it, you have no counter argument."

"But what if I get hungry?"

"I'll make you something."

"But this is my place, you know the pantry is full of books."

"Would you like me to go out and get us some breakfast?" Jess asked her, already preparing himself to get up.

"Oh would you? I guess I'll just wait for you here then," she laughed as she pulled the covers up over her head in preparation for the attack she knew was coming.

Jess surprised her by simply patting her head through the sheets and bidding her goodbye.

"I'll be back soon."

* * *

Jess took a lot longer than Rory expected and she began to get restless lazing around all alone in her bed. By the time he returned she was showered and dressed and sitting at the kitchen table waiting for him.

"What happened to the plan?" Jess asked as he put two overflowing grocery bags on the table in front of her.

"Felt wrong without you," she admitted.

"Well, I'm back now, do you want to..."

"Let's do something. I've been living here for over a year now and aside from my route to and from work and the location of every decent coffee stand along the way I still don't really know my way around. The last two times you stayed we didn't have much time but now we do and I'd love for you to be my tour guide," she watched Jess as he unpacked the food.

"Okay," he agreed.

Rory went back to her room and pulled out a guidebook she'd been keeping in her drawer but had yet to open.

"You won't be needing that," Jess assured her as he handed her a cup of coffee and a plate of toast. "You eat, I'm going to shower and then we'll go."

By the time they returned home late that evening Rory's feet were killing her. Jess had taken her to 3 different used book stores that she'd never have found on her own and one little hole in the wall record store she'd been to once before.

"Hey Jess?" she called out to him from the lounge.

"Yeah?"

"I think we should go with your plan for tomorrow."

"I'm going to hold you to that Gilmore. My back is killing me from carrying all your books."

"So I guess you won't be carrying me to bed tonight?" she looked up and saw him standing against the doorframe.

"That was a one off, don't expect that to happen ever again," he warned her.

"Thanks for today Jess."

"I'm going to bed now Rory," Jess moved toward the door to the guest room.

"You don't have to sleep in there if you don't want to," Rory told him, slightly confused by his motion.

"I know but I think I should. This thing only works if we stick by the rules right? I'm having a little trouble with number 4 right now."

"Oh." was all Rory could find to say.

"Goodbye Rory."

"Goodbye Jess."

She watched as he disappeared into the guest room, shutting the door behind him. Suddenly realising maybe she wasn't so clear on the forth rule herself anymore.

* * *

The next morning she found a note pushed under door.

 _I'm sorry but I can't stay._

 _J x_

The guest room was empty, the bed made, all trace of Jess gone. She sat on the bed with her arms wrapped around her body and sobbed, certain her heart would fall out of her chest if she didn't hold it in tight enough.

I'm sorry too Jess, she told the empty room.

I didn't mean to fall in love with you again either.


	11. Chapter 11

_**Present**_

"If I ask you a question will you answer me honestly?" Rory asked Jess, closing her book and placing it in her lap and waiting for him to do the same with his. They'd passed the halfway point of her stay and had found their way back to being comfortable with each other. There had been no more dates or innocent kisses since the picnic.

"That depends on the question," Jess finished his paragraph and looked up at her.

"How do you afford all of this? I mean, I know you wrote three books and you know I loved every word of them but you haven't had a book published in over 7 years and I know you don't have any other job. What's your secret Mariano?"

"What makes you think I've got a secret, Nancy?" he watched her curiously.

"I have a theory and I've been wondering how to prove it and I've decided that the most reliable way to solve any mystery is to go straight to the source," he didn't trust her in the slightest when she got that glimmer in her eye.

"Is that so? Maybe you should become an investigative reporter? Oh wait..." he teased her, trying to change the track of this conversation but she knew him too well to fall for that.

"I'm going to get to the bottom of this with or without your help," she threatened.

"Ask away Gilmore, no guarantee I'll answer but go ahead," he goaded her.

"Have you had any books published in the last 7 years?"

"Yes."

"Why haven't I read them?"

"How do you know you haven't?"

"So you write under a pen name?"

"That's one word for it."

"How many books have you had published under your pen name?"

"4. There's a fifth going through the final stages at the moment due out in a little over a month. The sixth is still a work in progress. You know the tapping sound that you hear coming from my office? I'm not practicing morse code," Jess knew she'd figure it out pretty quickly now but he'd kept it a secret long enough. Only one other person aside from his editor knew his secret and he'd threatened Lily's book collection if she ever let it be known and his editor was bound by a more official contract so it was pretty safe. If Rory hadn't found those damn copies under the bed they wouldn't be having this conversation right now.

"4?" she queried.

"You already know Rory. Just ask the question you really want to ask."

"Are you Elizabeth Johnson?"

"No." he smiled innocently at her.

"Is Elizabeth Johnson your pen name?" she tried again.

"Yes."

"I knew it! It had to be you. I admit it took me until the end of the first book before I started to wonder but I finished the last book this morning and there was no doubt in my mind you wrote them. It was just something about the way you wrote your sentences, your voice was coming through as I read. Romance novels Jess?"

"Please don't call me a sell out. I have to write that drivel so I can afford to take the time to work on the piece I've been struggling with for the last seven years." he tried to justify himself.

"You misunderstand me Jess, those books are not drivel, far from it. They're beautiful Jess. Just so incredibly beautiful. They made me laugh and cry and yearn and...squirm," Rory blushed amidst her excitement and held up the book in her lap to show him the cover. "I've already started reading them again from the beginning."

"You really like them that much?" Jess asked, genuinely surprised.

"I love them Jess. Who knew you were such a closet romantic? The dinner date and our picnic suddenly make more sense to me. You weren't pretending to be someone else you were just letting your real self out for a few hours. I can see why you'd want to keep your identity a secret, if word of this got out you'd have to go into protective custody," she continued to tease him but there was truth behind her words and that was what he heard.

"You remember when I told you I couldn't have written The Subsect without you? Your support and encouragement meant so much to me at that time in my life even if I had a funny way of showing it. I couldn't have written these books without you either but for slightly different reasons. The woman in the story is you. I couldn't give you the life you desired and deserved so I wrote a modern day fairytale for you instead," Jess told her a truth nobody else knew.

"Oh Jess," Rory started to speak but burst into tears instead. She'd shed more tears for this man than for every other hardship or happiness in her life combined.

"Hey, don't cry Rory. I don't want you to cry," he looked at her helplessly as the tears continued to flow but he didn't move to comfort her. "Would you like to read the next book? I have a preview copy."

He had her attention now.

"Yes please," she wiped the tears from her eyes.

"Wait here, I'll go get it," he left her on the lounge and went into his study. He took the book out of the envelope it had arrived in two days before Rory had landed on his doorstep. He hadn't been able to bring himself to look at it yet, not after she'd told him why she was here. Not after their two almost perfect dates. He opened the cover and picked up a pen to write a short inscription in the front.

 _You weren't the only one trying to tie up loose ends._

He stared at the ink on the page until the words began to blur and he realised it wasn't the letters moving but rather the tears in his eyes making them appear to be. He wiped them away and took the book to its new owner.

Rory looked up when Jess came back into the room. He passed the book to her, seemingly reluctant to let it go. He released his grip and gave her a half smile before turning and walking away.

"Goodbye Rory," he called back to her as he reached the front door, jacket in hand.

"Goodbye Jess," she watched him disappear until the plain ivory door filled the space he'd momentarily painted black.

She stared at the book in her hands, turning it over several times before opening it to the title page. She read the words he'd scrawled across the paper just minutes before then turned the page to find out if he'd written them a happy ending.


	12. Chapter 12

_**3 years earlier**_

"I guess I should have know it was you seeing as it's 2 in the morning. What's so important this time that it couldn't wait 5 more hours?" Jess grumbled sleepily at her as he let her in his front door.

"I just needed to see you. Needed to..." she attempted to explain but the tears she had been trying to contain for the last two days were now running in rivulets down her face and she was afraid that now the floodgates were open nothing would be able to stop them.

"Hey, come here," Jess wrapped his arms around her tightly not at all concerned about the tears soaking through his shirt only worrying about the reason for them.

"Where are your bags?" he asked as he went to shut the door, noticing for the first time she was in her old teacup pyjamas and she appeared to be empty handed. Rory didn't answer him but continued to sob against his chest.

"Hey, it's okay. Come with me," he led her into his room and tucked her into his bed, pulling a chair up to sit beside her. "You're scaring me here Rory, will you please try and tell me what's wrong?"

"I lost it. I never even got to tell you and I lost it," she choked out the words.

"What did you lose Rory? Whatever it was I'm sure we can find another one," he held her hand in both of his.

"You can't just go to the store and buy a baby."

"You were...?"

"8 weeks."

"Oh Rory, why didn't you tell me?"

"I had only just found out and I was going to tell you and then I lost it and I wasn't going to tell you at all but there's no one else I can tell because no one else knows about this thing we've been doing for the last 5 years and I thought I could handle this on my own but I couldn't. I don't know how to do this Jess. I feel like there's this enormous weight on my chest and I can't breath and it just keeps pressing me down and I feel so trapped and I feel so empty. It was barely bigger than a grain of rice but it's left this huge gaping hole," Rory had pulled her hand out of his grip and now had them placed protectively over the hollow place.

"I don't even know what to say Rory."

"There's nothing you can say."

"What can I do to help you? I can't stand to see you this way. I can't stand the thought that it's somehow my fault."

"Oh Jess, this isn't anyone's fault. It just wasn't meant to be," she repeated the words the kind nurse at the hospital had offered her even though she didn't really believe them herself. "Do you think you could just hold me until I fall asleep?"

He settled himself in the bed behind her, pulling her into his body and curling his limbs around hers.

"Rory?"

"Yes Jess?"

"It was really mine?"

"You know there's never been anyone else."

"I'm sorry this happened to you Rory."

"I don't think I've ever felt this sad before."

"Maybe it's for the best."

When Rory didn't respond Jess assumed she was asleep. He lay awake beside her, holding her safe in his arms, until the sun began to creep in around the edges of the curtains. He left Rory sleeping and went to the bathroom. With the steady drum of the water to drown out the sound he finally gave in and let himself cry for what they'd lost and then felt sick as he realised the tears of sorrow were mixed with tears of relief.

Later on in the morning his emotions took a different turn and he punched a hole in the living room wall. How could he be so irresponsible. He'd neglected to abide by rule number 2.

* * *

He remembered the night clearly, he'd been getting pressure from his new publicist to get out and meet some other writers and make some new contacts. It was the last thing he wanted to waste a Saturday night doing but Rory encouraged him to go and agreed to accompany him to a charity dinner in New York. Before the dessert dishes had even been cleared away they disappeared upstairs to the hotel room that had been booked as part of the dinner package. They'd both had far too much to drink, mostly because the speeches had been painfully dull but they'd been sitting for 2 hours so the effect hadn't really hit them until they were struggling to figure out how to make the key open the door.

"Green means go!" Rory was cheering him on. "Go go go go go Jess go. Oh man, too slow!"

He'd tried again and this time managed to coordinate the turning of the handle with the light.

"You did it! I knew you had it in you Mariano!" Rory launched herself at him causing him to stumble and they both ended up on the floor, their feet still in the hall.

"How much did you have to drink?" he asked her, not realising his own speech was slurring.

"Not much," she winked as she rolled off him, crawling the rest of the way into the room, her long skirt impeding her progress and forcing her to give up two feet from the bed.

Jess kicked the door shut with his foot and crawled after her, pushing the layers of her skirt up her legs as his hands made their way to the black lace she'd told him about during the entree.

They'd never even made it to the bed that night and woke up the next morning dishevelled but more or less fully clothed. Neither of them spoke about what had happened. They had showered and dressed and checked out of the hotel, the bed still perfectly pristine. Jess had taken her home then driven back to Philadelphia before that Sunday's sun had set. They'd said good bye but neither one had called the other. Last night was the first he'd heard from her since.

* * *

The sound of Jess's fist breaking the wall woke Rory and she called out to him from his bed, disoriented and afraid.

"I'm here Rory."

"What was that noise?" she was standing in the doorway now

"Just trying to make the place look a bit more lived in," he shrugged his shoulders, embarrassment washing over him as she saw the damage he'd done to the plaster.

"Can I borrow some clothes? I don't really want to drive home in these."

"Sure, take whatever you want. You can stay here a while..." he stopped when he saw an unreadable change in her eyes.

"No, I need to get back," she insisted coldly.

"Do you want me to drive you? I can catch the train back," he offered.

"I don't need you doing me anymore favours. I shouldn't have come here in the first place," she backed away from him as he stepped toward her.

He didn't understand this change in her but he knew her well enough to respect her need for space.

"Will you call me when you get there?"

"Sure."

Twenty minutes later she was showered and dressed in a pair of Jess's sweat pants and the old grey shirt from the drawer in her room, the guest room.

Her eyes looked dark and empty as he tried to hug her. She made no effort to stop him but she didn't return his embrace and he knew that something had shifted between them. Something they might never be able to fix.

"Goodbye Rory," he watched the lift doors close. She disappeared without saying anything at all.

* * *

Rory ignored his calls for the next two weeks and eventually he stopped trying to reach her. He contemplated driving to New York, letting himself into her apartment and waiting for her but he decided she just needed time. When he still hadn't heard from her after a month he got in his car and drove to the building she worked in. He parked a few blocks away then sat across the street, watching the door every time it glided open in case it was Rory walking through it. Eventually she did and he was relieved to see she was smiling. A tall blonde man was talking to her and something he said made her laugh and even though Jess couldn't hear it from his position across the street the noise stabbed painfully at his heart and he couldn't bring himself to move. When they were out of his field of view he made his way back to his car and got out of this city that had already seen too many damaging moments in his life.

He didn't bother trying to call her again but sent her a message, short and bitter and unable to be retracted once it was gone:

 _Looks like you forgot about rule number 3._

 _ **to be continued...**_

 _ **A/N I had to split this because it was getting too long (and sad) and it seemed right to break it here so I'll post both chapters together so you're not left hanging.**_


	13. Chapter 13

_**3 years earlier continued**_

How dare he? Was he spying on her? How _dare_ he! She read his message again for what must've been the sixteenth time that evening and before she could change her mind found his number in her mobile and hit the green button. He answered on the second ring and the sound of his voice sent an icy chill down her spine.

"So your phone does still work," Jess answered her cooly.

"Are you spying on me?" she demanded to know.

"Wouldn't have to if you'd just returned one of my calls," he jabbed back. "You come here, to Philadelphia, in the middle of the night, drop a tragic piece of news in my lap and then leave. I'm in the dark here Rory. Part of me thinks you're mad at me but I don't know why. Damn it Rory, you didn't even say goodbye."

"Yeah, well, seems like we've been breaking a few rules lately. Maybe it's a sign this thing between us has run its course." she told him bitterly.

"Convenient timing for you with a new blonde replacement already in the wings," Jess retorted.

"Geez Jess, I just met the guy yesterday. He's from Vancouver and was in town for a business meeting in my building and we bumped into each other on our way out the door. If that qualifies as cheating on you then I guess I'm guilty as charged," Rory was fuming and the words were out of her mouth before she'd had a chance to filter them. All the frustration she'd been pushing down for the last several months was finally coming to the surface. "I'd have to actually be with you though to cheat on you wouldn't I and you and I both know you've never been able to step up and make this something more. We broke the rules. What's done is done. You said it yourself: maybe it's for the best."

"When Rory? When did I say that?"

"I was right to be nervous about telling you about the baby. I knew it wasn't something you wanted."

"We never even talked about kids Rory."

"Well you don't usually make future plans with someone you're just fucking!" Rory shouted down the phone then hung up on him.

* * *

She could hear his voice on the answering machine but made no move to find the receiver.

"Rory, pick up the phone damnit."

"There were a lot of things we should've talked about Rory, I'm not the only one at fault here."

"We both broke the rules Rory. I fell in love with you in the midst of all this and I'm pretty sure you fell in love with me too but we were both too afraid to see what might happen if we spoke that truth out loud."

"Come on Rory, we need to talk about this. We need to fix this. 5 years Rory. I'm not going to let you throw that away because of some stupid misunderstanding."

"Rory, I didn't mean it when I said maybe it's for the best. I didn't know what to say."

"I hate talking to your fucking machine Rory, just pick up the damn phone."

The machine fell into silence for the first time in over an hour. Rory wiped away her tears and went in search of the portable handpiece and called him back.

"Are you still in love with me?" she asked when he answered.

"I don't know if there ever actually was a time when I wasn't," Jess admitted.

"Even the first time? What about the list? Specifically rule 4," she asked him, all the fight in her had dissipated with her tears and she now just felt sad and full of regret for all the time they'd wasted.

"Technically my feelings never changed."

"Oh."

"Do you remember the day we went to all those bookstores in New York?"

"Of course I do. I also remember you leaving in the middle of the night and not calling me for months afterwards."

"I almost told you that day. We were back in that record store and you turned around from the counter and it was like we'd gone back in time except you weren't wearing your plaid skirt and there was no cast on your arm and the words almost slipped out. I had to leave before I said something we'd both regret. I didn't call you because I needed time."

"You should've told me."

"Maybe. What difference would it have made? You've always been so busy and focused on your career Rory. As reluctant as you may have been initially, our arrangement suited you perfectly."

"I guess this baby was the proverbial spanner?"

"We were probably lucky it lasted as long as it did."

"What do you think would have happened if I hadn't lost it?"

"I really don't know Rory. I would have stood by you but you said yourself, we never discussed children. I've never been able to see myself as a father. Cool uncle maybe but a father? I'd hate to think what kind of issues I'd pass on to the next generation. I like my life, I like being able to come and go as I please, do what I want, when I want, hide in my office for weeks on end writing if inspiration hits. Does that sound like father material to you?"

"I guess not. Maybe it would have changed you though."

"And maybe I would've resented it for changing me."

"I want to have children Jess. I want to get married and buy a house in the suburbs and have a dog and a treehouse in the back yard and at least one, maybe two little cherubs to run through the sprinklers in the summer and build snowmen in the winter."

"Answer me this Rory, did you ever imagine me there with you? Which side of the white picket fence was I standing on? Was I staying or just passing through?"

"Oh Jess, I can't answer that because I honestly don't know. What I do know is when I found out I was pregnant I wanted that baby, your baby, more than anything I'd ever wanted in my life. I think you'd be a good father Jess but it sounds like we both want very different things. Maybe we should have had this conversation a long time ago."

"Maybe, but think of everything we would have missed out on in between," Jess smiled sadly.

"Does it seem strange to you that we are having the most important conversation of our relationship over the phone?" Rory asked him.

"In a way it makes sense. We always were good at the physical parts and bad at the emotional ones. I don't think we would have had this conversation if we'd been in the same room."

"Is this goodbye Jess?"

"I think it has to be, don't you?"

"But we can still be friends?"

"Give it some time Rory but yes, one day."

"I think I miss you already," Rory burst into tears again.

"I will always be here for you if you need me Rory. You will always be welcome to come and visit and stay. I do have a guest room as you might recall."

"Maybe I could come and stay with you for new year."

"That's over 7 months away Rory but yeah, sure. I'll keep the room spare for you. If you need me in the meantime, you know how to reach me."

"That works both ways Jess."

"I know."

"I love you Jess."

"I love you Rory."

"Goodbye Jess."

"Goodbye Rory."

 ** _A/N I thought I'd give you all a special Saturday night/Sunday treat. Hope you enjoyed these 4 chapters._**


	14. Chapter 14

_**Present**_

Rory was still up, waiting for him, when he returned home just after 1am. He could tell by the look on her face that she'd finished the book. He watched as she rose from the dining chair and made no attempt to move when she stepped in front of him and began to slide his jacket from his shoulders.

"Rory?"

"Shhh," she placed her finger over his lips to silence him then began to trace the contours of his face, as if trying to commit them to memory.

"Rory?" he held her wrists, moving her hands away. "What are you doing?"

 _"I make so many new beginnings there will never be an end,_ " she quoted to him.

"Jo March?"

"Yes."

"How does that explain what you're doing?" he pushed her hands away again as she reached for his shoulders.

"We can't tie up all the loose ends because we had too many beginnings. We never finished what we started. We've been ending every conversation for the last 7 plus years with goodbye but we never really meant it. I'm not trying to make a new beginning Jess but I think we deserve a proper ending, a genuine goodbye. Not one leaving us with a promise of next time. We need a goodbye that closes the door on that part of our life together so we can finally let it go and move on as friends."

"Were you going to ask me first or just seduce me in my kitchen?" Jess's head was spinning but somehow he thought she was making sense.

"Don't you get it Jess? I read the book. It was _you_ who asked _me_ remember?"

"But we aren't moving to the suburbs Rory. There's no white picket fence or dog or children in _our_ future."

"I know that Jess. I know that now. I also know that the reason I came here is because I can't have our last time together be some drunken entanglement on a hotel room floor. We deserve a better ending than that," she chanced to place a questioning kiss on his mouth.

At first Jess didn't respond but then he let his body take over and fell back into the beautiful comfort of kissing her. It had been 3 years but their bodies remembered the steps they'd each learnt by heart.

"Are you really sure about this?" Jess asked her as she worked her way down his buttons.

"I am," she undid the belt on her robe and Jess pushed the soft fabric off her shoulders watching as it pooled behind her on the floor like abandoned angel's wings.

"Are you sure about this?" Rory asked Jess when he paused, staring at the floor behind her.

"Not entirely but I want to do this anyway. I think your theory might be right but neither of us can know that for certain until tomorrow," he told her honestly.

They made out like teenagers eventually shedding the last of their clothes and then made love like it was the last time they'd ever get to because that was the truth of this night, this truly was the last time. They didn't need to wait for morning to know it, they felt it in their hearts and made the most of the precious time they did have left to indulge in each other.

* * *

"Part of me will always love you," Rory lay snuggled into Jess's side.

"And me you," Jess kissed the top of her head and tightened his grip around her back.

Neither of them were in any hurry to leave. This time goodbye really would mean goodbye.

They stayed in bed remembering the happy moments of their past together, both comforted by the knowledge that their happiest memories were ones of their friendship which had evolved with them over the last 15 years. They didn't have to say goodbye to that today.

"Will you still come to the wedding?" Rory dared to ask him.

"I already sent you my RSVP," he reminded her.

"But that was before."

"I accepted that invitation as one of your closest friends and even after all of this that connection still remains so yes Rory, I will still come to the wedding," he kissed her on the forehead.

"Thank you Jess. For that and for everything else."

"I've only ever wanted to see you happy Rory. Adam is a good guy and I can see you together in your fancy house, two kids and a dog," he admitted.

"And Uncle Jess coming to visit?"

"Yeah, I can see that too," he smiled at her. "Face it Gilmore, we're stuck with each other. Maybe not in the way you daydreamed about when you were 17 but, I don't know, I think maybe this might be even better."

They lay there quietly until Rory's stomach began to grumble causing them both to laugh.

"What time is it?" Rory asked and Jess reached over to pick up his watch from the nightstand.

"Huh."

"What?"

"It's 2 o'clock. I guess that's an appropriate time for us to finish what we started."

"That always has been our number," Rory agreed.

They found their clothes from the night before and with backs turned to each other got dressed.

Jess pulled Rory into one final embrace as they stood together in the doorway of his room, the threshold acting as an imaginary line between their past and future.

"It's been a pleasure loving you Rory," he whispered against her hair, not ready to let her go just yet.

"Thank you for helping us have a perfect goodbye," Rory whispered back.

Jess held her there until he felt a calmness settle over his body and then he let her go.

"Goodbye Rory."

"Goodbye Jess."


	15. Chapter 15

_**Two years earlier**_

"Hello?"

"Hi Jess, it's me, Rory.

"Hey. It's been a while."

"6 1/2 months."

"Are you calling to confirm your booking?"

"You remembered?"

"I told you I'd mark it on my calendar."

"The thing is, I was wondering if, I've kinda been seeing someone..."

"And you want to bring him?"

"Well, yes but I don't want you to feel like you have to say yes. It's your place, I don't want to impose."

"Is it serious?"

"Yeah."

"How long?"

"Um, a few months. We went out a few times but things didn't really get serious until he got a job transfer from Vancouver. He..."

"Works in your building now? Tall, blonde right? I sure can call 'em," he regretted his bitter tone as soon as he'd let it out.

"Oh, I'd forgotten about that. What do you mean by you sure can call 'em?" Rory asked, confused.

"I saw the way he made you laugh when you were going through the most difficult time of your life and he was virtually a stranger to you then. I can only imagine the way your face lights up for him now," Jess tried his best to keep his voice neutral.

"I have a feeling you might actually like this one Jess. Don't you think it's time we let each other go and moved on?"

"Sure."

"Hey, if it's a problem we won't come."

"Can you just let me think on it and get back to you?"

"Of course. I'll let you go."

"I'll call you."

"I know you will."

"Goodbye Rory."

"Goodbye Jess."

Jess hung up the phone and and went into the guest room. He picked up the only package he'd actually gone to the trouble of wrapping nicely this year, ribbon and all, and tore the blue and white snowflake paper to pieces. He pulled his old grey shirt out of the bottom drawer and tried to catch her scent on the soft ribbed cotton but it had been too long since she'd worn it and whatever had been left of her had been erased in the dark, empty drawer.

He lay on his back on the floor between the dresser and the bed, a set of four books on his chest. He wished they were heavier and that their combined weight would somehow crush him the way those five words out of Rory's mouth had crushed him - _I've kinda been seeing someone._ He rolled onto his side and pushed the books as far under the bed as he could reach then got up and went back to the only thing that had kept him sane over the last 6 months. He began to write and didn't stop until his aching fingers could no longer hold his pen. If this was the only way he could have her in his life then this would have to be enough.

* * *

Three days later he called her back.

"What time will you get here and if you say 2 o'clock the answer's no."

"Really? It's okay with you?" she sounded genuinely surprised.

"I told you you're welcome here anytime, I never said you had to come alone." he reasoned.

"I'll call you next week and let you know our plans," Rory's voice was light and happy.

"You've still got your key anyway right?"

"No, I lost it. I lost a lot of important things that month," the happy tone was gone.

"Well maybe you'll find a new one when you get here," Jess tried to comfort her but he'd never really been very good at that part. If he had maybe they wouldn't have ended up like this.

"I can live without a key. The most important thing I lost that month was you. Will I find my best friend when I get there?" The question was almost a whisper but Jess heard her.

"He'll be here waiting to give you your new key," he promised.

* * *

Their visit wasn't anywhere near as awkward as anyone had anticipated it to be. Rory had been right, Jess and Adam got along relatively well considering the circumstances.

Adam went to bed early the first night of their stay having been up early for work and then driven to Philly straight from the office. Jess was thankful to have a chance to speak to Rory alone.

"So, what exactly does he know about me cause I'm guessing not much seeing as though he hasn't made a single dagger eyed look all night. He hasn't even mocked me or asked me where I went to college. I'm not used to you dating a guy who's not a total jerk." Jess cracked open two beers and passed one to Rory who was sitting at one end of the lounge.

"Not all my ex boyfriends were jerks," she pointed out as he settled himself into the armchair.

"Um Rory, they kinda were, myself included, although I like to believe I redeemed myself at some point," he sipped the cool liquid and sank back against the backrest.

"Well, agreeing to let us stay was definitely not jerk-like behaviour. Maybe you have redeemed yourself, after all," Rory teased him.

"Geez Rory, that hurts!" he found himself laughing and it was a good feeling, sitting here, talking with her like this.

"Do you think I'd have wasted 5 years with you if you were a jerk Jess? Two maybe, three max but not 5," she asked.

"But technically we were never even together for any of that time," he pointed out.

"Do you honestly see it that way?" she caught his eyes and didn't shift her gaze until he finally answered her.

"I guess not," he sighed.

"I told him everything," she admitted, answering Jess's earlier question.

"Everything everything or just everything?"

"Everything everything."

"Huh."

"I think he's going to ask me to marry him."

"Huh."

"I think I'm going to say yes."

"Huh."

"Nothing else you want to say?"

"What do you expect me to say Rory? What do you want me to say?" Jess was struggling to conceal his cards here, his voice was beginning to rise and would soon give him away.

"I don't know," she spoke so softly now and he regretted his reaction.

"Let me know when it's official I'll be sure to tell you congratulations," a peace offering that fell short of sincerity.

"Jess please don't be like this," she pleaded.

"Like what Rory? Shocked? Surprised? Upset? Do you want me to jump up and down and squeal with excitement? I can give you the directions back to Stars hollow if that's the kind of reaction you were hoping for. They'll probably erect a statue in Adam's honour praising the brave knight who saved the princess from the savage stable boy," he snapped at her.

Rory began to giggle.

"What's so funny?" he demanded.

"You should write harlequin romance novels, that's a hell of a plot line you just spun - savage stable boy," Rory continued to giggle.

"Romance novels huh?" Jess took another sip of his beer.

"I'm sorry I haven't called you."

"It's okay Rory, I get it. I didn't call you either, remember?"

"Are you happy Jess?"

"I'm working on it. What about you?"

"I really am."

"That's a good thing Rory. You deserve to be happy."

"So do you Jess."

"I'm pretty happy right now. Sometimes I think you're the only person that I actually like to talk to. It's good to have you here," he admitted.

"Oh Jess, that's the saddest thing I've ever heard."

"It's not sad Rory, just true. Maybe one great friend is enough for me."

"Well then I guess you're stuck with me Mariano. Someone's got to make sure you don't turn into a hermit."

"I prefer recluse," Jess attempted a smile.

"Loner?"

"Ascetic."

"Jess?"

"Rory?"

"I don't regret any of it."

"I hear that's a good way to live life," Jess looked at her blankly. He had regrets but he didn't want to delve into them tonight.

They sat in silence for a little while, sipping on their beer, each lost in their own thoughts. It was Jess who eventually spoke first.

"So you really think he's going to pop the big question?" Jess dared to ask.

"I found a ring in his sock drawer," Rory admitted sheepishly.

"And you don't think it's too soon?"

"You know that saying - when you know you know? Turns out to actually be true," Rory shrugged sadly.

"Huh. Can't argue with that kind of logic," Jess finished his beer and stood up from the armchair, stretching his back as he did. A yawn escaped him and he checked his watch to see how late it was.

"Well would you look at that," he held the watch out for Rory to see.

"2am?"

"2am."

"Goodbye Jess." Rory rose and stepped toward the guest room.

"Goodbye Rory." Jess turned the handle to his door.

Were they ever going to truly be able to tear up those stupid rules?

 ** _A/N just a warning to let you know the next chapter is the last but will be followed by an epilogue._**


	16. Chapter 16

**_Present_**

Rory shut the guest room door behind her and began to gather together her belongings. Her two weeks weren't over yet but she'd done what she'd come here to do. She couldn't have known it would end this way but she couldn't have hoped for a better parting. She trusted their friendship could survive this. It would take time but it was the way it had to be. She hoped Jess would find happiness of his own one day. She'd never been able to mend all the broken parts of him. He'd already been broken when they first met and she had never been able to heal those scars but she felt like they'd at least managed to fix the ones they'd inflicted on each other over the years.

Jess stripped the sheets from his bed and loaded them into the washing machine. He figured Rory was probably packing to leave. It was time. In the past he wouldn't have washed the sheets until her scent had worn off but there was never going to be a next time now and so he set the machine in motion to spin all traces of her away. He kept himself busy by making sandwiches. He packed Rory's into the picnic hamper and added an apple and some biscuits for her drive home.

"Time to go then?" he observed her bags as she opened the door to her room. His guest room. Maybe it was time he started inviting other people over to stay so it wouldn't always seem to belong to her.

"Can I keep these?" she asked, holding up four books in her hand.

"As long as you can keep my secret then they're yours," he agreed.

"I can and I will, I promise."

"I packed you some food for the drive, I'll help you get all this down to your car," he picked up the bag he'd remembered being the heaviest when she arrived, he never had taken her up on her offer to read her books. It seemed lighter now and he looked at her questioningly.

"I left a few behind. Most of them were yours anyway," she explained.

Between the two of them it only took one trip to pack the car and Jess had a sudden urge to beg her to stay but he knew it would be the wrong thing to do and it would ruin the perfect bookend they'd created together last night.

"So, I guess the next time I'll see you will be at the wedding?" he asked instead.

"I'll be the one in white," Rory nodded, squinting her eyes as the afternoon sun pierced them with its glow.

"Let me know you get home safe?"

"I will."

"See you later Rory."

"See you later Jess."

Jess stood on the sidewalk until her car disappeared around a corner then went back up to his apartment. He stood in the doorway of the guest room and smiled when he saw she'd stripped the bed and left the sheets in a pile on the end of the mattress. He checked the bottom drawer already knowing his old grey shirt would be gone. In its place were at least a dozen books. He opened the next drawer and there were more there too and in the top one as well. He ran his finger over the spines, smiling as he remembered Rory's indignation when he'd stolen her copy of Howl and written in its margins. Who was the book thief now? He lay down on the bare mattress, resting his head on the pillow that still smelled like her and let out a sigh that could almost be described as contented. He reached across and selected the thin paperback that had started it all and began to read.

 ** _A/N this is the final chapter. I'll have the epilogue up soon. This might seem wrong to leave them this way but they will always be in each other's lives just in a different way to what we'd ideally like. I hope I've portrayed this realistically enough that you can understand how I came to end it like this._**

 ** _Thanks to everyone who has read this story and especially those who've taken the time to review._**

 ** _Special thanks to Jordana60 who faithfully reviewed this story the first time around and again this time - I tweaked the epilogue for you, it's a small change but I hope you like it._**

 ** _If you're looking for a happier ending for these two I have other lit fics on my page that will hopefully give you what you're after._**

 ** _Lastly, I've decided I will write an alternate ending for this story but will post it as a separate piece so keep an eye out for it in the near future._**


	17. Chapter 17

**Epilogue**

 ** _2 weeks later_**

As Jess watched her from his seat in the second row he felt an unfamiliar peace settle over him. The feeling didn't surprise him but was the opposite of how he would've have expected to feel about this moment a month ago. Now he felt free. All the loose ends had been tied up. He no longer had a mind full of what ifs or regrets. He would always love this woman but he knew for sure now that they were never meant to be together forever. It was time for him to find some happiness of his own.

He rose as the crowd around him rose. He smiled as she reached his row and she met his eyes and smiled back. She had never looked more beautiful to him and he had never felt more happy for her. Whatever else happened in their lives they would always have a bittersweet ending to remember and a lifetime of friendship still to experience.

* * *

 ** _2 months later_**

He rang the doorbell and stood back to wait for someone to answer it, chuckling to himself as he turned away to take in the picket fence and perfect lawn he'd just crossed. He turned back to the door when he heard it opening, metal scraping against wood.

"Hey! You're here early!" Rory smiled excitedly, hugging him tightly but briefly.

"Nice fence," Jess nodded his head in its direction.

"Do you like it? White seemed too much of a cliche so we painted it blue instead."

She was still smiling and Jess couldn't help but smile back at her. She was happy and in that moment the anxiety he'd felt over this reunion dissipated and he realised he was happy too.

"Here, this is for you and Adam, housewarming present," he pushed a bottle of wine into her hand, "and this is for you."

Rory studied the thick envelope he'd been hiding behind his back, curiosity etched in her sparkling eyes.

"I finally finished it. Took me long enough," he shrugged with false nonchalance and placed his hard earned pages in her hands.

Rory unsealed the package and removed the pile of paper, studying the type on the cover sheet.

"Dispelling Cliches by Jess Mariano...You did it!" She squealed in excitement, throwing her arms around him for another quick hug. "You wrote another book! Too bad I'm expecting a bunch of people to arrive soon for this housewarming party, I want to go and read it right now!"

"Don't get too excited Rory, it's only a first draft," he tried to quell her enthusiasm but he could feel pride swelling in his chest at her reaction.

"Can I give you notes?"

"I'd be disappointed if you didn't."

"I'm so proud of you Jess."

"Are you going to invite me in or do I only get a tour of your front porch?"

"Well, it is a nice porch..." Rory teased. "Of course you can come in. Adam's in the kitchen, come say hello to him first then I'll show you around."

Jess followed her though the front door and down a long hallway to a large open plan kitchen with double doors leading out onto a back patio.

"Hey Jess, good to see you," Adam greeted him with a handshake. "Glad you could make it."

"Glad to be here," Jess replied sincerely.

"Jess brought this for us," Rory held out the bottle of wine and Adam took it from her, placing a kiss on her cheek while she was in close enough range.

"Thanks Jess, shall we open it now?" Adam offered.

"Not on my account, I can't stay long and it's a long drive back," Jess declined.

"You can't stay?" Rory asked, a slight pout curving her lower lip.

"I came early in the hope that it wouldn't matter so much if I left early," Jess explained.

"Well in that case, I better hurry up and give you the tour," Rory was back on Jess's side of the kitchen bench. She looked across to Adam, steadily working his way through a pile of vegetables for the salad, "you all good here hun? You don't mind if I leave you to do all this while I show Jess around?"

"Nothing would make me happier than if you left me to this Rory, you and I, and Jess too I'm sure, all know how little help to me you are on this side of the counter," Adam laughed at the look of indignation on his wife's face. "You also know I love you despite your complete lack of culinary skills."

"Well I am particularly good at the cleaning up part," she reminded him.

"We do make a good team, now get out of the kitchen. I know you've been dying to show Jess the study. If you haven't returned but the time the rest of our guests arrive I'll know where to find you," Adam smiled at Rory and she nodded in agreement before leading Jess out of the kitchen to begin the tour.

Rory saved the study for last as it was her favourite room in the house and she knew Jess would love it too. Three of the walls were a lush olive green and the forth was taken up completely by bookshelves that Luke had lovingly installed for her. A desk sat in front of the window with a view over the backyard and a large sofa took up the wall opposite the books.

"They're not full yet but that is my goal," Rory stood next to the shelves, running her fingers over the spines.

Jess stepped closer and skimmed over her collection, smiling when he noticed 5 Elizabeth Johnson novels standing side by side.

"So you bought a copy?" he asked her, pointing to the fifth one that had only come out a few weeks earlier.

"I've still got the original but it didn't seem right to put it out here on the shelf. It's packed away for safe keeping along with your secret," she explained.

"This is a great place you've got for yourselves here Rory. A great life. I really am happy for you," he changed the subject. He looked out the window across the backyard and could easily imagine a couple of kids running around out there.

"Hey Jess, just because I've moved doesn't change the fact that you're always welcome whenever you need a place to stay if you're going to be in the city or even just because," she watched him as he turned away from the window. "The couch is actually a sofa bed. This would be your room if you ever..."

"I appreciate the offer Rory, maybe someday I'll take you and Adam up on it," he began to walk towards the door.

"Will you at least stay for some lunch?" she asked him when they were back in the hall.

"Well I wasn't planning on it but now that I know Adam made all the food I will," he teased her and copped a fist to his arm as punishment.

"You still punch like a girl," he laughed as she rubbed her bruised knuckles.

They walked back into the kitchen laughing and Rory sat and watched as Jess pitched in and helped Adam finish preparing the lunch until the rest of the guests arrived.

* * *

 ** _2 years later_**

"So if you both die I have to raise your kid?" Jess was attempting to clarify the details before he committed to anything.

"Well no, that would be Lane," Rory reminded him. This was the third time they'd been over this but the christening was tomorrow and he was yet to give them an answer.

"But what if Lane dies?" he asked.

"Well then yes, in the extremely unlikely event that both Adam and I and Lane pass away and Nate is still under legal age, you will have to raise him," she explained.

"And you're really sure you want me to be that person?"

"Think of it as more of an Uncle Jess kind of role than a potential back up father. There's no one else I'd rather have as godfather to my son," Rory assured him.

"What about Luke?" Jess's reasons to say no were quickly running out. None of them had been substantial in the first place really. Truth be told he'd been honoured when Adam and Rory asked him when he'd gone to visit them in hospital the day after Nate was born. He'd told them he'd think about it but that was months ago and he still hadn't committed to it.

"He's already Poppy," Rory reminded him. Jess laughed at the name as he did everytime he heard it. It had been Lorelai's idea of course and it had stuck even though the kid wouldn't be able to call his step-grandfather by any name at all for at least another year.

"I guess our family tree is already confusing enough," Jess reasoned.

"You're our first and only choice for Godfather Jess," Rory was almost at the point of pleading.

"Well I guess I'd better say yes then," he finally relented.

"Really Jess? You're saying yes?" she asked him excitedly.

"Yes Rory, I will be Nate's godfather," Jess accepted.

"Oh Jess, thank you. This really means so much to me. To Adam too. To both of us," she hugged him tightly and kissed him on the cheek before letting him go.

"Remember this moment when Nate starts quoting Hemingway to you," Jess laughed at the look of concern that passed across Rory's face. Maybe being godfather would be a pretty cool role to have after all.

* * *

 ** _20 years later_**

"Can you believe he's graduating? It seems like just last week you were visiting the three of us in the hospital!" Rory hugged Jess as he met them out the front of the auditorium.

"Nate's going to be so happy you made it," Adam reached out his hand to shake Jess's. "He was a bit disappointed when he found out Anna couldn't make it."

"Her book is doing so well they decided to tack on a few more dates to her press tour. She was sad to miss out on seeing our nephew graduate but she knows Lorelai well enough to expect a reenactment when we are back down next month. I was just talking to Nate yesterday, he called for some advice on his speech, I wouldn't have missed this for anything," Jess assured him, taking his hand in his and patting him on the shoulder with his free one.

"Mum and Luke are inside saving us seats. Shall we go on in?" Rory asked, bouncing nervously beside them.

"How much coffee have you had this morning Gilmore?" Jess had never stopped calling her by her maiden name more out of habit then for any Freudian reason.

"I cut her off after her third but I suspect Lorelai snuck a flask in her oversized purse and has been sneaking her sips while I wasn't looking," Adam informed him.

"Ah, some things never change," Jess smiled.

The three of them entered the auditorium together and Adam lead the way down towards the front where Luke and Lorelai were waiting for them.

"Hey Jess! Good to see you!" Luke rose from his seat and hugged his nephew.

"Good to see you too Poppy," Jess hugged him back.

"I thought we'd decided you were never going to call me that again," Luke spoke through gritted teeth.

"I recall a discussion but not a decision," Jess ducked in anticipation of the smack on the head coming his way.

"Hey you two, no fighting today!" Lorelai stood and took her turn hugging Jess. "I'm glad you could make it. I've got my camera ready to capture all the important moments for Anna. I guess you should probably get used to flying solo at these kind of things now that your wife has a Booker prize stamp on the front of her novel."

"I've barely seen her in the last month but I'm so proud of her. She really earned that accolade," Jess smiled warmly as he spoke of his wife.

"I hear you helped Nate out with his speech, that was nice of you."

"Seemed a god-fatherly thing to do," Jess shrugged off her praise as he returned the hug.

"You've been a good one Jess. To Nate and to Jane," Lorelai smiled and let him take the seat between herself and Rory.

They chatted amongst themselves while they waited for the ceremony to start. Once it was underway they nodded along with the speeches, feigning interest, but they were only really looking forward to listening to Nate.

Lorelai and Rory whistled and yelled as Nate took his place at the podium, blushing as he spotted his family in the crowd.

"My mother was valedictorian when she graduated from her high school and my great grandfather used to love to tell me about the wonderful speech she had made that day so I feel like I've got some pretty big shoes to fill standing up here today, as valedictorian of my own graduating class, and if my words have even a fraction of the impact hers had then I'll feel like I did my job here well.

This school has taught me everything I could hope to learn from within the pages of our text books and the challenging minds of our teachers and that knowledge has been supplemented by the influences and experiences of my family and friends.

The branches of my family tree may intersect in unusual ways but every limb has had a role in shaping the person I am today. They are my shelter from the storms, my support when I lack the strength to hold my head high, and my shade on those days when I'm searching for a quiet place to rest away from the burning sun. They've taught me the valuable lesson that sometimes you have to shed your old leaves and that the new growth will be bolder and brighter than the ones that had dwelled there for too long before. Change is not something to be afraid of but something to embrace as it pushes you forward along paths you may not have chosen to venture down had they remained hidden by a perennial canopy.

I'd like to finish with a quote from Little Women by Louisa May Alcott. This book was read to me by many different voices and these words meant different things to each of them:

" _I keep turning over new leaves, and spoiling them, as I used to spoil my copybooks; and I make so many beginnings there never will be an end."_

On this day, when we are about to embark on our own separate journeys away from the comfort and security we've found within these halls and classrooms, I hope we can all go forward and embrace every new beginning that comes our way."

Jess was the first to rise to his feet, applauding proudly as Nate finished his speech. Lorelai and Rory had tissues to their eyes as they stood up beside him, each with their respective husband's arm wrapped protectively around their waists, wiping their own proud tears away with the backs of their hands.

Jess stood in between the two couples and reflected on Nate's words, smiling as he recognised that these people were his branches too. He reached his arms wide across Rory's back to his right and Lorelai's to his left, his hands resting on Adam and Luke's shoulders, tying them all together, tears of happiness flowing freely down his face.

* * *

 ** _A/N and that's the end of this story (with possibly the longest epilogue ever). Wow! Five days and I'm done. What a rollercoaster ride this has been for me as a writer! When I couldn't get to sleep Monday night and decided to try and write a new story instead I had no idea it would end up here._** ** _I hope you've enjoyed this little journey. It was definitely a different experience writing them this way but I'm glad I did._**

 ** _Thanks as always for reading and thank you especially to those of you who took the time to review._**

 ** _Please let me know what you think of the ending and remember to check out the alternate ending link on my profile._**

 ** _I will likely be back at some point but the next one is going to have to be pretty fluffy to make up for this one so consider yourself forewarned._**

 ** _Until then..._**


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